(R)-3-FORMYL-3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLIC ACID TERT-BUTYL ESTER synthesis

8synthesis methods

Product Name:(R)-3-FORMYL-3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLIC ACID TERT-BUTYL ESTER
CAS Number:444583-19-1
Molecular formula:C15H19NO3
Molecular Weight:261.32

2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-3-[(methoxymethylamino)carbonyl]-, 1,1-dimethylethyl ester, (3R)-

444583-18-0
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(R)-3-FORMYL-3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLIC ACID TERT-BUTYL ESTER

444583-19-1
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Yield:444583-19-1 100%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran;diethyl ether at 0; for 1 h;

Steps:

214.B Step B.; (3R)-tert-Butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Lithium aluminum hydride (1 M in THF, 5.3 ml, 5.3 mmol) was added to a solution of (3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1.7 g, 5.0 mmol theory) in ether (16 ml) stirring at 0° C. under nitrogen. After stirring at 0° C. for 1 h, the reaction was slowly quenched with water (0.40 ml). Sodium hydroxide (1N, 0.80 ml) followed by water (0.60 ml) were then added and the resultant gelatinous precipitate was filtered through Celite rinsing with ether and THF. The filtrate was evaporated and the residue transferred to a separatory funnel with EtOAc. Washing with brine and drying with MgSO₄afforded crude product (1.3 g, 100% yield) which was used in the next step without further purification

References:

US2005/80074,2005,A1 Location in patent:Page/Page column 72

845543-81-9 Synthesis